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We help you gain critical insights and make more informed decisions across your business priorities.Dark Reading Resource LibraryBlack Hat NewsOmdia CybersecurityAdvertiseNewsletter Sign-UpNewsletter Sign-UpCybersecurity TopicsRelated TopicsApplication SecurityCybersecurity CareersCloud SecurityCyber RiskCyberattacks & Data BreachesCybersecurity AnalyticsCybersecurity OperationsData PrivacyEndpoint SecurityICS/OT SecurityIdentity & Access Mgmt SecurityInsider ThreatsIoTMobile SecurityPerimeterPhysical SecurityRemote WorkforceThreat IntelligenceVulnerabilities & ThreatsRecent in Cybersecurity TopicsThreat IntelligenceAI-Assisted Exploit Development Outpaces Scanner DetectionAI-Assisted Exploit Development Outpaces Scanner DetectionbyElizabeth MontalbanoMay 27, 20265 Min ReadApplication SecurityFeeding Frenzy: 'Megalodon' Malware Infects Thousands of GitHub ReposFeeding Frenzy: 'Megalodon' Malware Infects Thousands of GitHub ReposbyRob WrightMay 26, 20264 Min ReadWorld Related TopicsDR GlobalMiddle East & AfricaAsia PacificLatin AmericaSee AllThe EdgeDR TechnologyEventsRelated TopicsUpcoming EventsPodcastsWebinarsSEE ALLResourcesRelated TopicsResource LibraryNewslettersPodcastsReportsVideosWebinarsWhite PapersHeard It From a CISOReporters' NotebookDark Reading's 20thPartner PerspectivesMeet the EditorsAdvertise With Us About UsDark Reading Resource LibraryCyber RiskCybersecurity OperationsCybersecurity AnalyticsEndpoint SecurityNewsCybersecurity In-Depth: Feature articles on security strategy, latest trends, and people to know.Focus on Cyber Insurance: How Quantifying Risk Is Reshaping SecurityIn this latest installment of the Reporters' Notebook video series, we discuss how cyber insurance is forcing organizations to quantify risk, what's covered (and what's not), and why this could be the best thing to happen to cybersecurity.Fahmida Y. Rashid,Kristina BeekMay 28, 2026Source: Dark ReadingCyber insurance has evolved from a niche product into a critical component of enterprise risk management, fundamentally changing how organizations approach cybersecurity. Unlike traditional property insurance, cyber insurance faces adversaries whose tactics are constantly evolving. These attackers are becoming more sophisticated and have more tools at their disposal than ever before.The cyber insurance market has matured significantly over the past three decades and now encompasses coverage for breach remediation costs, regulatory penalties, business interruption losses and cyber extortion payments. But perhaps more importantly, cyber insurance is forcing a long-overdue conversation about the true cost of cyberattacks. By attaching actual numbers to previously abstracted risks, insurers are compelling organizations to move beyond vague concerns about "getting breached" to understanding specific financial impacts and operational disruptions.Related:How CISOs Should Prep for Agentic-Ready AI BOMsHowever, this safety net comes with an unexpected consequence: insured companies are more likely to pay ransomware demands. Threat actors take the time to identify which organizations carry cyber insurance and for how much, then calibrate their demands accordingly. When attackers know a company is insured for $10 million, they can make a compelling business case to pay the ransom to avoid $50 million in business losses. This creates a troubling dynamic in which insurance, designed to protect organizations, may actually incentivize the very attacks it's meant to mitigate. This risk quantification is reshaping the entire cybersecurity landscape in other ways as well. Insurance providers now require organizations to maintain minimum security standards—such as multi-factor authentication, proper data backups and documented incident response protocols—or risk having their claims denied. Three reporters—Dark Reading's Fahmida Y. Rashid, TechTarget SearchSecurity's Richard Livingston, and Cybersecurity Dive's David Jones — open up their notebooks to share insights on how cyber insurance is evolving, what the declining premiums really mean, and how this particular safety net is simultaneously making organizations more vulnerable to ransomware and improving their overall security posture.Learn more in the video transcript below, and check out other episodes in the Reporters' Notebook series for insights and coverage from across Informa TechTarget's three cybersecurity publications.Fahmida Y. Rashid, Richard Livingston & David Jones: Full Video TranscriptThis transcript has been edited for clarity and length by Informa TechTarget's internal AI assistant. For the full experience, please watch the video.Related:Checkbox Assessments Aren't Fit to Measure RiskDark Reading's Fahmida Y. Rashid: Hi and welcome to our latest edition of Reporters' Notebook. I'm Fahmida Rashid, managing editor of technology and features at Dark Reading, and I'm joined here with my counterparts from Cybersecurity Dive and TechTarget SearchSecurity. I'll have everyone introduce themselves. So, Richard, why don't you take it away?TechTarget SearchSecurity's Richard Livingston: Hi, I'm Richard Livingston. I'm a writer and editor with TechTarget SearchSecurity.Cybersecurity Dive's David Jones: I'm David Jones. I'm a reporter with Cybersecurity Dive.DR's Fahmida Y. Rashid: And for this month's Reporters' Notebook, we are going to be digging into cyber insurance. I feel like that is a term that everyone is talking about. All three of us have written a lot about the topic, and there's just so much that doesn't quite surface in people's consciousness. Richard, let's just start right off. What is cyber insurance? What is it? What is it covering? What is it for?TTSS's Richard Livingston: Yeah, so I read a great quote the other day, and this is a unique thing, right? It's not like property insurance. I heard a great quote that said, for property insurance, fires are not trying to figure out better ways to burn you. And with cyber insurance, what we're trying to actually do is cover a risk that is trying to override your security protocols. And I think all of us know that this is getting worse, that hackers are getting more sophisticated.Related:Research Hub Bridges Cybersecurity Gap for Under-Resourced OrganizationsThey have more tools at their disposal. Really over the last 30 years or so now, cyber insurance has matured to the point where we now have a market that for businesses that rely on data in the cloud, which is pretty much just about everybody. They are covering now remediation services, and that's the costs of responding to a breach, forensics, legal fees, PR, you name it.Information security and privacy liability, the claims and damages from a breach. Regulatory defense and penalties, all the fees and the penalties and the legal costs that can come from a regulatory action if you find a damaging breach. The business interruption, the lost revenue that you're going to see there. Media liability, this could be a reputational problem too. And then also the big one is cyber extortion. We have hackers asking for ransom and people are paying.DR's Fahmida Y. Rashid: I do want to know before we go on further, a couple years ago I was having a conversation with security expert Jeremiah Grossman and one of the things he said is the fact that we have cyber insurance is actually going to be the good thing for cybersecurity because we're finally attaching numbers, we're finally quantifying. Before it was like, we don't want to get breached, we don't know how much it costs or what the impact is. And now that the insurance companies are coming in and they're saying, no, we can't be loosey goosey here. We need to know what the impact is. We need to know what it's going to cost to get, you know, back up and running. What are your liabilities? And it's going to change how we talk about cybersecurity. Just now when you were running through all the things insurance covered, that's exactly what was reminding me that I don't think five years ago we would have even talked about liability in the context of an attack.TTSS's Richard Livingston: Yeah, well, you know — what's insurance? Basically claims and actuarial tables. And, you know, as long as there is a business model for them, they're going to keep putting out coverage there, you know, as long as they can keep getting those premiums and they're making more money than they're paying out. You know, there's your business model.DR's Fahmida Y. Rashid: I know, Dave, we were talking a little bit about what IT insurance covered. You had some really interesting insights there on what is covered or not covered and what those big questions are.CD's David Jones: Yeah, I mean, think what has evolved over the years is that companies are starting to really understand how cyber risk impacts the bottom line of their businesses, where it's not just, you know, a corporate CISO or an IT manager that is dealing with the fallout of a cyberattack or business disruption related to cyber. I think that what you're seeing now is that companies are now dealing with not just the potential loss of data, but they're dealing with the potential disruption of their business function. So essentially what you have is a company may, you know, have some kind of a breach or some type of a ransomware event or other type of disruption where they functionally cannot operate for a period of hours, days, or weeks at a time. And in certain cases, they can't operate kinetically. They have to shut down their factories or their connections where they have an IoT connection with various partner companies. They may not be able to sell their product.We ran into that with companies like JLR. There were other companies that had to deal with weeks long disruptions of their operations where they couldn't move their product. And one of things that cyber allows you to do is you can kind of price in the potential risk of what would happen if I basically could not move my product or operate my business for a series of weeks or days. And you have to be able to estimate, OK, let's say I'm out of business for a week. If you go back to like Colonial Pipeline, for example, you basically can't move your fuel for almost a week. What kind of bottom-line impact is that gonna have on my business?And how do I factor in the risk of being able to manage that? And the insurance companies at the same time, what they do is they force you to take a really hard look at how am I prepared to be resilient? What am I doing to protect our business in the event of where I can't get into my data, my employees can't get on their computers? I can't move my product to and from a warehouse. And cyber insurance will basically force you to look at how do you back up your data? How do you access your data in the event of a shutdown? What type of protocols you put in place? Multifactor, hiding assets from the Internet, using stronger passwords and they will force you to make some very tough decisions about, you know, do I have the resources set aside where I may be going back to a very low tech version of my business for a couple of weeks.DR's Fahmida Y. Rashid: I do want to know, I know I think it was last Black Hat, there were the whole session kind of touching on what you were saying, like how do you prove to the insurance company that you've done what you're supposed to do? Like insurance companies, like, "Hey, you have to make sure you have a certain baseline." And, you know, before what you had to do an audit and now with questionnaires or some kind of a way where they can look at your control. So that conversation has also been evolving where insurance companies want you to prove before a breach that you've done everything you need to do to make sure you can recover, that you're resilient. And that is also an area that seems still a little uncertain. No one seems to have that magical formula of this is how you prove it.TTSS's Richard Livingston: Yeah, but it's interesting. Those are being put into the policies. There are requirements in there, and there have been situations where claims have been denied. If people did not keep up a certain minimum level of security. A few years ago, Hamilton, Ontario, the city, got breached, and they were fully insured. But hackers got in because they did not maintain a minimum level of MFA. And they got in, and when auditors looked at it, they said, nope, know, this is clearly spelled out in your contract. And the taxpayers of Hamilton, Ontario, got hit with that whole thing.DR's Fahmida Y. Rashid: Yeah, you know, reading that fine print, it's always, that's always where you get tripped up in these kind of things.TTSS's Richard Livingston: And that's why other parts of the organization, besides CISOs, need to be involved, right? You need your legal teams on there. You need your analysts. This is question of more people in the organization. This is really not so much a technical issue. It is a risk issue. And that's the whole C-suite's business.DR's Fahmida Y. Rashid: And I know Cybersecurity Dive had done a lot of coverage on that changing language of risk. Dave, I think it's also worth kind of talking about the awareness from the organization perspective, what is covered, what is not covered, and what did that language of risk mean? So, I know you've done a bit recently on that.CD's David Jones: Yeah, I mean, it's evolved over the years. You know, if you go back, you know, about a decade back, there were some fairly high profile incidents where during, you know, cases like NotPetya and WannaCry, there were, you know, propagating cyber cases where various companies from different parts of the world were impacted by these propagating events. And you basically had a situation where these companies were on the hook for hundreds of millions of dollars where they couldn't function for a certain amount of time. And there were events that were kinetic disputes involving Russia, involving Ukraine. And there were questions raised because one of the things that cyber insurance has historically limited is if you are impacted during what is considered an act of war and there were cases in the past where if the attackers had some state-linked connections, arm of an intelligence service or military service and you were attacked in that type of an environment you had to fight to get covered. [It’s not] necessarily [where] you wouldn't get any coverage but the insurance companies could put some major limitations on what they were going to pay out and you know what we're seeing now with the Iran war for example you know we're seeing this kind of thing pop up in other forms of insurance you know you have ships that can't you know get oil and move into other parts of the world. You have cyberattacks that are being linked to state actors and it's impacting the ability of companies to manufacture their products, to fulfill orders, to ship their products. In some cases, customers hear about an attack and they automatically disconnect. I mean, we saw that with Striker where hospitals and healthcare providers that were, when they became aware of what happened, they, just as a form of precaution, they basically disconnected their services. And so, you had situations and some of these cases where you can't perform surgeries, appointments are canceled, customers are just basically in the dark until they find out if it's safe to restart their operations. And so, we've had cases in recent years where years-long battles between insurance companies and claimants, policyholders, in terms of how much of this claim, because we're talking hundreds of millions of dollars in claims, and the insurance companies don't want to be on the hook for hundreds of millions of dollars, especially if they're not sure that the proper protocols were taken to protect core assets. You know, there have been discussions among policyholders, among insurance companies about whether the global insurance industry is prepared for some type of potentially catastrophic event. You know, we saw concerns raised after the CrowdStrike outage from a couple of years back, whether the industry can sustain some type of systemic event where multiple companies are impacted by some type of propagating malware or global outage or supply chain event. And we're seeing more and more of these cases where third party companies are impacted, and they can impact dozens or hundreds of companies at the same time.DR's Fahmida Y. Rashid: Supply chain is always one of those where we don't always think about the blast radius. I think insurance companies are having to start thinking about that blast radius. Like one company gets breached and now you have 12 other customers filing claims because that one company got breached. And I don't think insurance insurers have really figured out how they're going to handle that yet. Like it's 12 different claims, what are you going to do? You can't really say, you shouldn't have worked with these companies. I think that's an area that we're going to keep hearing insurance companies evolve in their thinking. Richard, I know since we're running a little tight on time, I wanted to actually kind of point back to this really cool insight you had on the downside of insurance.TTSS's Richard Livingston: So, I actually sat in a really interesting session at RSAC and John Kindervag, the Zero Trust guy was there. He started off with this really compelling argument. He said, you know, the rise in life insurance put a financial layer on a very ancient crime, murder.It didn't increase murders, but all of sudden now people had a financial benefit there. So, let's look at ransomware the same way and what we're seeing. Here's a data point that he gave us that — the companies that are insured for cybersecurity, are 2.8 times more likely to go ahead and pay out their ransomware request. So, what we're seeing is that hackers, have at their disposal the Dark Web. They can find out who is insured and for how much. And in many cases, what they're doing is they are going to organizations. And when they lock up their systems, they're saying, you know what? We know that you are insured for $10 million. If you told me right now that you would pay us $10 million, we won't ask for a cent more. And that's, the point that he made is that, you know, they're a business like you're a business. And if it's a matter of paying out $10 million to save yourself $50 million worth of, you know, business losses, you know, that's a, you know, I think that's a negotiation most companies are willing to have. And they are, they're paying.DR's Fahmida Y. Rashid: And I think a lot of the time when we talk about, know, this is a bit of a tangent, but when people talk about should we pay the ransom or not paying the ransom, you're right, insurance changes that calculus a little bit. Like, well, it's not coming out of my pocket. So, this is why we are buying insurance, right? Like we buy insurance for accidents and catastrophes. So, it definitely does add a second layer to that. I think the other thing when we were talking about this topic, all three of us were discussing just the fact that with insurance providers, overall rates, like how much it costs to get insurance, has been declining slightly for the past two years. And I know for me, I was just like, this is great. This means more companies are going to buy insurance. But I think there is also a downside to lower costs.And, you know, Dave, I think you were expressing some of those concerns about, what does it mean if policies are cheaper? And Richard, I think you had some thoughts on that as well.CD's David Jones: I mean, I think that there have been concerns raised by the industry that when you're in a market where risk seems to be exponentially kind of increasing of larger scale events, and there's a concern about concentration risk where the global insurance market is very heavily weighted towards the US. Both in terms of the number of companies that are in the US and the global industry, basically two thirds of the market is kind of based here in the US. Large companies, you get some kind of systemic event that affects multiple companies at the same time, and you have a situation where one event can kind of tilt the balance. And so, you run into a situation where companies, insurance companies are trying to diversify their portfolios a bit. They'd like to get smaller and medium-sized companies into their portfolios. They'd like to get companies that are based outside of the US because the penetration of the market in other parts of the world, there are a lot of companies out there that could probably benefit from insurance that aren't covered, or maybe they self-insure, or maybe they have policies that are property or casually or some other type of policies where there is a cyber component, but if there's a really catastrophic event, do they have the adequate amount of coverage? And one of the things that insurance does for the overall market is it forces a lot of these companies to take their own internal practices more seriously, because the insurance companies will force you to do it.They're not just going to give you a free check based on you neglecting your hygiene or neglecting your training or neglecting your overall IT stack and then expecting that the insurance company is going to cover all your losses. What's happening is that you're starting to see a lot of these companies, they're taking a much closer look in terms of making sure that policyholders are taking the steps necessary to get everybody in the company involved in the process. For example, is the board of directors involved? Are the C-suite people involved? Does everybody know if there's a ransomware attack, who's going to be responding to that emergency and the role that each individual will play in responding to that? You know, depending on how companies, you know, manage that process, you're going to see some adjustments in terms of how those companies pay out those claims. And you're not going to just see insurance companies write a blank check for a company that's not kind of taking care of its own responsibilities and expecting that they're going to be covered.I think that if you look at what's happening now with things like AI implementation, a lot of companies are rolling out agentic AI without the proper guardrails set up where they understand the risks, where they have the proper governance set up with committees, with rules about whether an employee can experiment with AI or use AI in their day-to-day work environment. What happens if there is a company or an employee that's using an AI and an unsanctioned agent and there's a huge catastrophic leak of data or disruption of the business? Companies have to, you know — insurers are going to look at that and they have to now price another level of risk in terms of, you know, are we going to pay for a situation where a company rolled out technology, did not have guardrails in place to prepare for some type of an emergency, and things are moving so quickly in that space? That has to be something that responsible financial governments and banks and investors are going to take a very hard look at.TTSS's Richard Livingston: I think that's a good thing. If you're giving companies a safety net, but at the same time really making them examine their cybersecurity and putting better practices in place, that's good for everybody.DR's Fahmida Y. Rashid: So, we're going to call it time. Thank you so much for tuning in to Reporters' Notebook. I'm Fahmida Rashid, managing editor from Dark Reading, and thanks for joining us. Dave, Richard, can you say your good-byes?TTSS's Richard Livingston: Yep, I'm Richard Livingston from TechTarget Search Security.CD's David Jones: Thanks for listening, I'm Dave Jones at Cybersecurity Dive.About the AuthorsFahmida Y. RashidManaging Editor, Technology & Features, Dark ReadingFahmida Y Rashid is an award-winning B2B cybersecurity journalist with over two decades of experience covering enterprise technology. As Dark Reading's managing editor for technology and features, Fahmida Y Rashid focuses on stories that provide security professionals with the information that goes beyond the day's headlines. She breaks down news events and industry trends to demystify security technology for IT professionals, cybersecurity practitioners, and business managers. She takes an interdisciplinary approach to explain security concepts through the lens of psychology and economics. She also analyzes data to uncover insights to help CISOs do their jobs.Areas of focus include: application security; cloud, network, and infrastructure security; identity and access management; third-party and supply chain risk; governance and compliance; and cybersecurity data analytics.Her work has appeared in various business and tech trade publications, including CSO Online, InfoWorld, and eWEEK. Previously, she was the Executive Editor at VentureBeat, where she led the newsroom as part of its transition to focus on AI and data technologies. She co-founded the cybersecurity magazine Decipher and was the editor-in-chief of RSAC Conference. Prior to specializing in information security, she covered enterprise IT, especially networking, open source, and core internet infrastructure at Forbes.com and CRN. She also reviewed networking technologies as an analyst at CRN Test Center and PCMag.Before becoming a journalist, she spent over 10 years as an IT professional, and has experience as a network administrator, database administrator, software developer, management consultant, and product manager. Fahmida Y Rashid holds a master's degree in journalism and a certificate in computational journalism from Columbia University Graduate School of Journalism. Her work has earned multiple Azbee awards from the American Society of Business Publication Editors, including recognition for her feature reporting on how linguistics can be used to uncover the cyberattackers' origins.BlueSky: https://bsky.app/profile/fyrashid.bsky.socialMastodon: @[email protected]See more from Fahmida Y. RashidKristina BeekAssociate Editor, Dark ReadingKristina Beek is associate editor at Dark Reading, where she covers a wide range of cybersecurity topics and spearheads video-related content, where she contributes both content and production skills to Dark Reading's expanding video coverage. She is the creator and host of the Heard It From a CISO video series, where she interviews CISOs, directors, and other industry strategists to provide insights into the ever-evolving cybersecurity landscape. In addition to her editorial work, Kristina manages Dark Reading's social media channels (including social video), and has held numerous roles within Dark Reading over the years, including copy editor and breaking news reporter, before transitioning her focus to multimedia journalism.Kristina graduated from North Carolina State University in 2021 with a degree in Political Science, concentrating in law and justice, and a minor in English. During her time at NC State, she honed her writing skills by contributing opinion pieces to the university's newspaper, as well as writing fiction, poetry, and short essays. 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Cyber insurance has transitioned from a niche offering into a critical component of enterprise risk management, fundamentally altering how organizations approach cybersecurity. Unlike traditional property insurance, cyber insurance addresses risks posed by evolving and sophisticated adversaries, compelling the market to quantify the true financial and operational costs associated with cyber incidents. This quantification forces organizations to move beyond abstract concerns about a mere breach to understand specific financial impacts and operational disruptions, thereby reshaping cybersecurity strategy.

The scope of cyber insurance now encompasses coverage for breach remediation costs, regulatory penalties, business interruption losses, and cyber extortion payments. This expansion has driven a necessary conversation about the true cost of cyberattacks by attaching concrete figures to previously intangible risks. This dynamic creates a significant consequence: insured companies are observed to be more likely to comply with ransomware demands because threat actors can leverage insurance data to negotiate demands, recognizing that paying a ransom may be less costly than facing the full spectrum of business interruption losses.

Furthermore, the involvement of insurers exerts pressure on organizations to improve their security posture. To avoid claim denials, insurance providers mandate that entities maintain minimum security standards, including implementing multi-factor authentication, ensuring proper data backups, and establishing documented incident response protocols. This requirement shifts the focus from purely technical security measures to overall organizational resilience.

Insights gathered by reporters indicate that this process of quantification is also advancing security. By attaching financial liability to incidents, insurance compels organizations to assess their preparedness for operational disruption stemming from security failures. This involves estimating the impact of being unable to operate kinetic functions, such as halting production or accessing critical systems, which demands that organizations evaluate backup capabilities, data access protocols, and operational continuity plans. This forces organizations to implement stronger preventative controls, such as multi-factor authentication and reduced exposure of assets online.

The evolving framework also touches on broader systemic risks. Discussions have emerged regarding the liability surrounding cyberattacks, particularly in contexts involving state actors or supply chain disruptions, where insurance coverage can be limited or contested. There is also concern among the insurance industry about handling catastrophic, widespread events, such as large-scale malware propagation or global outages, prompting a need to assess the industry's ability to sustain systemic risks.

The role of cyber insurance necessitates broader organizational involvement beyond the Chief Information Security Officer. Because cyber risk is fundamentally a business issue, involving legal teams and the C-suite is crucial for managing the fallout, assessing liability, and ensuring that risk mitigation strategies are integrated across the organization.

As technology evolves, such as the integration of agentic artificial intelligence, the scrutiny from insurers is expected to intensify. Insurers will be compelled to price in the risks associated with deploying new technologies without adequate governance, guardrails, and risk assessments. This means evaluating whether organizations have established committees, rules, and protocols for using AI in day-to-day operations to ensure that potential catastrophic data leaks or operational disruptions are accounted for in policy risk calculations. Ultimately, the existence of cyber insurance serves as a mechanism forcing organizations to adopt a more proactive, risk-aware, and resilient approach to cybersecurity.